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Chiral aminomethylnaphthols have been prepared highly diastereoselective by means of three-component “Betti condensation”, using steroidal 2-naphthol analogue, synthesized from estrone. The use of 2-methoxybenzaldehyde or 2-pyridinecarboxaldehyde as aldehyde component and (S)-(–)-1-phenylethan-1-amine or (S)-(–)-1-(naphthalen-2-yl)ethan-1-amine, as chiral non-racemic amine component providing the diastereoselectivity, allowed the synthesis of structurally diverse aminomethylnaphthols. The latter easily form 1,3-dihydronaphthoxazines through reaction with formaldehyde. The absolute configurations of the new aminomethylnaphthols synthesized have been determined through advanced nuclear magnetic resonance (NMR) experiments and confirmed by X-ray crystallography. The chiral steroidal aminomethylnaphthols obtained as pure diastereoisomers have been evaluated as pre-catalysts in the enantioselective addition of diethylzinc to aldehydes with enantioselectivities of up to 97% ee.

A series of 42 diarylethers and their analogues were synthesized. All compounds were tested in vitro against six viruses. Two diarylethers in this series demonstrated selective and remarkable activity toward Human Coronavirus OC43 and Human Adenovirus 5 (SI 97.4 and 99.7, respectively). QSARs for the investigated antiviral activities were explored. The analysis was based on a large library of 113 diarylethers and their analogues comprising the compounds reported in this paper, as well as compounds previously synthesized and tested by us. Statistically reliable regression and discriminant models were derived which revealed structural and physicochemical features of the compounds important for the antiviral activities. These models may be used as guidance for synthesis of lead compounds with promising antiviral activity toward the investigated viruses.